CA1043818A - Process for the production of aromatic trifluoromethyl compounds of the benzene series - Google Patents
Process for the production of aromatic trifluoromethyl compounds of the benzene seriesInfo
- Publication number
- CA1043818A CA1043818A CA241,944A CA241944A CA1043818A CA 1043818 A CA1043818 A CA 1043818A CA 241944 A CA241944 A CA 241944A CA 1043818 A CA1043818 A CA 1043818A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- trichloromethyl
- reaction
- benzene series
- hydrogen fluoride
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 238000000034 method Methods 0.000 title claims abstract description 29
- 238000004519 manufacturing process Methods 0.000 title claims abstract description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 title claims 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 46
- -1 TRIFLUOROMETHYL COMPOUNDS Chemical class 0.000 claims abstract description 20
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 claims abstract description 18
- 229910000040 hydrogen fluoride Inorganic materials 0.000 claims abstract description 18
- 239000003054 catalyst Substances 0.000 claims abstract description 15
- VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 claims abstract description 11
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims abstract description 9
- 238000004821 distillation Methods 0.000 claims description 3
- FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 claims description 3
- 150000001555 benzenes Chemical class 0.000 abstract description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical class C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 6
- 230000035484 reaction time Effects 0.000 description 6
- GETTZEONDQJALK-UHFFFAOYSA-N (trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1 GETTZEONDQJALK-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 239000000306 component Substances 0.000 description 3
- 238000005260 corrosion Methods 0.000 description 3
- 230000007797 corrosion Effects 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- XEMRAKSQROQPBR-UHFFFAOYSA-N (trichloromethyl)benzene Chemical compound ClC(Cl)(Cl)C1=CC=CC=C1 XEMRAKSQROQPBR-UHFFFAOYSA-N 0.000 description 2
- PDCBZHHORLHNCZ-UHFFFAOYSA-N 1,4-bis(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C=C1 PDCBZHHORLHNCZ-UHFFFAOYSA-N 0.000 description 2
- DGRVQOKCSKDWIH-UHFFFAOYSA-N 1-chloro-2-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC=C1Cl DGRVQOKCSKDWIH-UHFFFAOYSA-N 0.000 description 2
- KALSHRGEFLVFHE-UHFFFAOYSA-N 2,4-dichloro-1-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1Cl KALSHRGEFLVFHE-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 238000004587 chromatography analysis Methods 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- QULYNCCPRWKEMF-UHFFFAOYSA-N parachlorobenzotrifluoride Chemical compound FC(F)(F)C1=CC=C(Cl)C=C1 QULYNCCPRWKEMF-UHFFFAOYSA-N 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- QZPROWPVBAXNOK-UHFFFAOYSA-N 1,2,4-tris(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(C(F)(F)F)C(C(F)(F)F)=C1 QZPROWPVBAXNOK-UHFFFAOYSA-N 0.000 description 1
- YTCGOUNVIAWCMG-UHFFFAOYSA-N 1-chloro-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(Cl)=C1 YTCGOUNVIAWCMG-UHFFFAOYSA-N 0.000 description 1
- LVZPKYYPPLUECL-UHFFFAOYSA-N 1-chloro-4-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C=C1 LVZPKYYPPLUECL-UHFFFAOYSA-N 0.000 description 1
- KZSNBJMYJWDVTK-UHFFFAOYSA-N 2,4-dichloro-1-(trichloromethyl)benzene Chemical compound ClC1=CC=C(C(Cl)(Cl)Cl)C(Cl)=C1 KZSNBJMYJWDVTK-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-M Fluoride anion Chemical compound [F-] KRHYYFGTRYWZRS-UHFFFAOYSA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- 229940058905 antimony compound for treatment of leishmaniasis and trypanosomiasis Drugs 0.000 description 1
- 150000001463 antimony compounds Chemical class 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 239000012267 brine Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000008030 elimination Effects 0.000 description 1
- 238000003379 elimination reaction Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N ferric oxide Chemical compound O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 238000003780 insertion Methods 0.000 description 1
- 230000037431 insertion Effects 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C17/00—Preparation of halogenated hydrocarbons
- C07C17/093—Preparation of halogenated hydrocarbons by replacement by halogens
- C07C17/20—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms
- C07C17/202—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction
- C07C17/206—Preparation of halogenated hydrocarbons by replacement by halogens of halogen atoms by other halogen atoms two or more compounds being involved in the reaction the other compound being HX
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1687274A CH598163A5 (enrdf_load_stackoverflow) | 1974-12-19 | 1974-12-19 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1043818A true CA1043818A (en) | 1978-12-05 |
Family
ID=4420969
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA241,944A Expired CA1043818A (en) | 1974-12-19 | 1975-12-17 | Process for the production of aromatic trifluoromethyl compounds of the benzene series |
Country Status (15)
Families Citing this family (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2546532C2 (de) * | 1975-10-17 | 1977-11-17 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Trichlormethyl-trifluormethylbenzolen |
| JPS6039048B2 (ja) * | 1976-12-27 | 1985-09-04 | ダイキン工業株式会社 | ベンゾトリフルオライドまたはその誘導体の製法 |
| US4393257A (en) * | 1976-12-27 | 1983-07-12 | Daikin Kogyo Co., Ltd. | Process for preparing benzotrifluoride and its derivatives |
| JPS5382728A (en) * | 1976-12-27 | 1978-07-21 | Daikin Ind Ltd | Fluorination of lower alkylbenzene or its dervs. |
| DE2708190C2 (de) * | 1977-02-25 | 1984-09-27 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von m-Brom-benzotrifluoriden |
| FR2478074A1 (fr) * | 1980-03-17 | 1981-09-18 | Rhone Poulenc Ind | Procede de preparation de trifluoromethylbenzenes a partir des trichloro- ou tribromo-methylbenzenes correspondants |
| US4367348A (en) * | 1980-10-10 | 1983-01-04 | Occidental Chemical Corporation | Novel trifluoromethyl benzal chlorides and process for the preparation thereof |
| US4876404A (en) * | 1986-08-13 | 1989-10-24 | Central Glass Company, Limited | Preparation of dichlorotrifluoromethyltoluenes including novel isomers |
| CN102320919B (zh) * | 2011-10-31 | 2014-07-23 | 江苏威耳化工有限公司 | 2，6-二氯-三氟甲苯的制备方法 |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2562159A (en) * | 1944-11-30 | 1951-07-24 | Bruno H Wojcik | Production of xylene hexafluoride |
| US2654789A (en) * | 1948-03-12 | 1953-10-06 | Ethyl Corp | New chlorofluoro derivatives of cyclohexane and method of making same |
| CH580551A5 (enrdf_load_stackoverflow) * | 1973-12-21 | 1976-10-15 | Lonza Ag |
-
1974
- 1974-12-19 CH CH1687274A patent/CH598163A5/xx not_active IP Right Cessation
-
1975
- 1975-01-20 DE DE19752502092 patent/DE2502092A1/de not_active Withdrawn
- 1975-12-03 IE IE2637/75A patent/IE42368B1/en unknown
- 1975-12-04 NL NL7514146A patent/NL7514146A/xx not_active Application Discontinuation
- 1975-12-08 GB GB5018175A patent/GB1472370A/en not_active Expired
- 1975-12-11 IT IT52627/75A patent/IT1052802B/it active
- 1975-12-17 CA CA241,944A patent/CA1043818A/en not_active Expired
- 1975-12-17 SE SE7514302A patent/SE7514302L/xx unknown
- 1975-12-17 DK DK573975AA patent/DK138888B/da unknown
- 1975-12-17 US US05/641,778 patent/US4080392A/en not_active Expired - Lifetime
- 1975-12-17 SU SU752198554A patent/SU606547A3/ru active
- 1975-12-18 BR BR7508409*A patent/BR7508409A/pt unknown
- 1975-12-19 LU LU74080A patent/LU74080A1/xx unknown
- 1975-12-19 FR FR7539130A patent/FR2295004A1/fr active Granted
- 1975-12-19 BE BE162956A patent/BE836889A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| IT1052802B (it) | 1981-07-20 |
| FR2295004A1 (fr) | 1976-07-16 |
| LU74080A1 (enrdf_load_stackoverflow) | 1976-11-11 |
| GB1472370A (en) | 1977-05-04 |
| US4080392A (en) | 1978-03-21 |
| IE42368B1 (en) | 1980-07-30 |
| DK573975A (enrdf_load_stackoverflow) | 1976-06-20 |
| DE2502092A1 (de) | 1976-07-01 |
| CH598163A5 (enrdf_load_stackoverflow) | 1978-04-28 |
| DK138888B (da) | 1978-11-13 |
| SU606547A3 (ru) | 1978-05-05 |
| SE7514302L (sv) | 1976-06-21 |
| FR2295004B1 (enrdf_load_stackoverflow) | 1980-08-14 |
| IE42368L (en) | 1976-06-19 |
| NL7514146A (nl) | 1976-06-22 |
| DK138888C (enrdf_load_stackoverflow) | 1979-04-30 |
| BE836889A (fr) | 1976-06-21 |
| BR7508409A (pt) | 1976-08-24 |
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